Winchester Travel Guide

Tourist Guide

Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.
Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.
Aerial view of Winchester Center Historic District and First Congregational Church panorama in downtown Winchester, Massachusetts, USA.
Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA.
Skyline of Boston
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
Stay at this hotel in Boston. Enjoy free Wi-Fi, a 24-hour front desk and a business centre. Our guests praise the breakfast and the restaurant in their reviews. ...
9.2/10 Wonderful! (6,288 reviews)
very clean room. excellent staff very accommodating….

Reviewed on 17 Feb 2026

Get rates
Harborside Inn Of Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Stay at this hotel in Boston. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the restaurant and the helpful staff in ...
9/10 Wonderful! (2,479 reviews)
The room and shared bathrooms were perfect

Reviewed on 17 Feb 2026

Get rates
The Revolution Hotel
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St Boston MA
The price is Rp6.140.760 per night from 19 Feb to 20 Feb
Rp6.140.760
Rp7.150.917 total
19 Feb - 20 Feb
includes taxes & fees
Stay at this luxury hotel in Boston. Enjoy free Wi-Fi, breakfast (surcharge) and room service. Our guests praise the helpful staff and the clean rooms in their ...
9.6/10 Exceptional! (1,004 reviews)
They were very family friendly. The pool was great. This is our fourth third or fourth time staying there and my girls absolutely love it… They always make an effort to do an upgrade if they can or make your visit special we absolutely love staying there.

Reviewed on 17 Feb 2026

The Langham, Boston
See all 4,181 properties in Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
8 Harrison Ave Boston MA
Stay at this business-friendly aparthotel in Boston. Enjoy free Wi-Fi, a 24-hour front desk and a 24-hour business centre. Our guests praise the helpful staff ...
8/10 Very Good! (659 reviews)
Great location and very helpful font desk staff. The room was clean and had everything we needed. Could use a little maintenence but honestly for the price, you really can't beat it.

Reviewed on 14 Feb 2026

Global Luxury Suites Downtown Boston
Temple Place Suites

Temple Place Suites

2.5 out of 5
29 Temple Place Boston MA
Stay at this apartment in Boston. Enjoy free Wi-Fi, laundry facilities and cable TV channels. Popular attractions Boston Common and New England Aquarium are ...
7/10 Good! (332 reviews)
Very spacious

Reviewed on 15 Feb 2026

Temple Place Suites
Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway

3 out of 5
28 Fenway Boston MA
Stay at this apartment in Boston. Enjoy free Wi-Fi, laundry facilities and concierge services. Popular attractions Fenway Park and Copley Square are located ...
8.6/10 Excellent! (337 reviews)
I stayed here for an extended stay after relocation from my apartment. I had been staying in the same unit and it was not expressed as to for my second extension I was to be relocated. I received a call in the middle of the work day saying I needed to move all my stuff. I was met with a rude temperament ...

Reviewed on 31 Jan 2026

Maverick Suites at 28 Fenway
See all properties in Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theatre scene and great live music.

Gillette Stadium
Boston Common which includes a skyscraper, landscape views and a park

Boston Common

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common
Harvard University showing a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston's Zakim Bridge

TD Garden

Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.

TD Garden
New England Aquarium featuring marine life

New England Aquarium

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

Rp882.157
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Step into a festive winter oasis at Stratus bar this holiday season! Adorned with glittering icicles, sparkling lights, and festive winter elements, this experience is a must must-visit.

View Boston Observation Deck Admission Tickets

Rp571.880
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

Rp386.860
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

Rp1.328.780
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

Rp759.591
per adult
100% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

Rp1.412.880
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Winchester

Cities near Winchester

Quincy Market showing a city, an administrative buidling and heritage architecture

Boston